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Actionable Roleplaying Tips: Engaging Your Companions

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Alright. Ready to sink your teeth into a good roleplaying topic? I think this is one of my favorite ones.

Inter-party discussions is one of the most interesting roleplaying opportunities in the game. In this post, you’ll find a few suggestions on how to instigate such discussions as well as prepare for them.

Before we get started, however, let’s quickly revisit the purpose of this whole series. Here’s a quote from the first post.

How do I take some actionable steps to prepare to roleplay?

Sharing the my answers to that question is the purpose of this four-part post series. I’m not suggesting this is the best course of action for everyone. All I know is that it worked for me. It gave me something actionable. It got me started. I’m having a blast playing these characters. So if that helps you or another reader, the purpose of these posts is fulfilled.

Caught up? Awesome. Here are the past posts if you want to catch up and future posts for a little preview.

So, how do you engage your companions? Questions. It starts with questions. But what questions do you ask?

Who, What, When, Where and How

Starting a conversation when roleplaying starts the same way that it does in real life. You ask questions. Start with questions that reveal the historical background of the companion. Here are a few starters.

Where are you from? What was it like there?

What did you do before adventuring? How long ago was that? Who trained you?

Did you have family there? Other close people? Are they still there?

Getting answers to these questions is great. It gives your character some insight into the factual background of other characters. But does it really help you get to know them? Really know them? Well. No.

Let me give you an example. During my first 12 years out of college, I moved from Lexington KY to Dallas TX to Houston TX to Detroit MI to Boston MA.

You now know something factual about me. But do you really have a glimpse into who I am? How I tick? What motivates me? No. Not really. You just know I moved around a bit.

Having the answers to these questions, however, enables your character to ask better questions. The Why questions.

Follow Up Why Questions

Why did I move from KY?

Well, I lived my whole life in KY, flying for the first time I went to interview for this awesome job in Dallas TX. Single, young and ambitious, I jumped at the opportunity to work for a small technology company. I drove my truck pulling a UHAUL trailer by myself for 16 hours for the move. I promised myself I would not fail in this job, working ridiculous hours, traveling the country and busting my tail while I did it. Looking back, that period of my life taught me I could do a lot. I gained confidence that was the foundation of my entire career. It was difficult, but I wouldn’t trade that experience for anything. Not for anything.

Now, you know something about me.

In a roleplaying game, how do you apply this idea? Just follow up your ‘who, what’, when, where and how’ questions with a ‘why’ question.

Why did you leave your home? Don’t you miss it?

Why did you leave your training? What happened to your master?

Why did you not follow in your father’s footsteps professionally?

This will help you understand more about your character companions. It will reveal some of their core motivations. It will instigate deeper converations.

More Why Questions

When it comes to getting into this kind of conversation during a roleplaying game, there’s another super-easy way to get the ball rolling: ask questions about why the character made life choices. Let me go deeper with that.

During character creation, players make key decisions including:

Class Selection

Background Selection

Equipment Selection

Most of this will be obvious to your character. So you can easily ask about it. These might be questions like:

So why did you become a warrior? You seem a little slight for it. Thieving might have suited you better.

Wizardy? It requires so much arcane study. How do you stand it… reading books constantly.

Why did you choose to following Deneir (or any other deity)? Most priests are so uppity. Why are you different?

Ah… the glaive. Personally, I would have picked a Great Axe. You know. A huge one. Why the glaive?

A frog for familiar? Crows are great because they can fly. Cats sneak. But a frog? Really?

Wait. You were a hermit? Alone. All the time. First, that’s kinda crazy. But why did you leave?

A criminal! You stole stuff? Wow. Why did you choose that kind of life?

OK. So you were a noble. Riches beyond measure. And you choose ADVENTURING? Seriously?

Cartography. You like drawing maps. Ummm… why? Its all just trees.

You play dice? *whispers* Are they loaded? Aren’t you afraid of getting caught?

Just think about character creation. There are lots of choices a player has to make. Each one of those choices is a great opportunity to reveal some insight into the psyche of the character.

Sharing: Connect over Common Experiences

What is left to do? Well, do what you do in the real world. If someone mentions something where there is some familiarity, share why that is familiar and your experience with it.

If a character has lost a family member and your character has as well, it is a great opportunity to share that. Explain the circumstance. Explain your character’s experience.

If a character explains why they have a frog familiar, maybe explain how your character had a pet boar on the farm. It was fierce but loyal. Explain your character’s experience.

If a character recites some of their deity’s dogma and believes, state if your character agree or disagree. That is an opportunity to express their worldview. Take advantage of it.

If a character has an unusual hobby, bring our your character’s hobby and share why it is a passion. Explain your character’s experience.

Actionable Takeaways

OK. So how do we make this actionable. Prepare to answer these questions for your character.

Figure out the what, when, where and how of your character. This is likely tied up in their formal background and bonds.

More importantly, write down or sentence or two about why your character made decisions in his past.

For your character’s class, equipment and other choices, come up with a reason why the character made that choice.

Be familiar with your character’s ideals, bonds and flaws.

Next, prepare to ask these questions of one or more player characters in your group.

Write down 3-4 questions that are what, when, where and how related to another character.

Be prepared to ask why for each one of those.

For each other character in the party, write down two questions related to class, background, equipment or some other decision the player made about that character.

There you go. That’s my advice. It may not be the best, but it works for me.